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Triethylamine → N-[6-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]norbornan-2-yl]pyrrolidine-1-carboxamide

HRID 75050
Notes
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Reaction equation

HRID 75050 reaction equation
[F:1][C:2]1[C:3]([NH:18][CH:19]2[CH:24]3[CH2:25][CH:21]([CH2:22][CH:23]3C(O)=O)[CH2:20]2)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1.C([N:31]([CH2:34]C)CC)C.N(P(OC1C=CC=CC=1)(OC1C=CC=CC=1)=[O:40])=[N+]=[N-].[NH:55]1[CH2:59][CH2:58][CH2:57][CH2:56]1>C1COCC1>[F:1][C:2]1[C:3]([NH:18][CH:19]2[CH:24]3[CH2:25][CH:21]([CH2:22][CH:23]3[NH:31][C:34]([N:55]3[CH2:59][CH2:58][CH2:57][CH2:56]3)=[O:40])[CH2:20]2)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 123414Diphenylphosphoryl azideHCID 672850466-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]norbornane-2-carboxylic acid2×

Product 1

HCID 67285331N-[6-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]norbornan-2-yl]pyrrolidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 6-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]norbornane-2-carboxylic acid, 72j, (0.030 g, 0.078 mmol) in THF (0.375 mL) was added triethylamine (0.032 mL, 0.234 mmol) and (azido(phenoxy)phosphoryl)oxybenzene (0.018 mL, 0.085 mmol). The reaction mixture was heated to 95° C. for 2.5 hours, cooled down to 5° C., and treated with pyrrolidine (0.010 mL, 0.117 mmol). The reaction was stirred for 3 days at room temperature. The reaction mixture was injected directly into a preparatory HPLC system for purification to provide the product as a racemic mixture. The single enantiomers were obtained by separation using SFC chiral purification to afford 5.7 mg of the desired product as well as 1.4 mg of the enantiomer.

Workup

  1. temperaturecooled down to 5° C.
  2. customThe reaction mixture was injected directly into a preparatory HPLC system for purification
  3. customto provide the product as a racemic mixture
  4. customThe single enantiomers were obtained by separation
  5. customSFC chiral purification

Sources & evidence

ORD record
ord-aa97cbb4c5e741fc98e91b27da276cfd
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829007B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes